586-06-1

• 常用中文名：奥西那林
• 常用英文名：orciprenaline
• CAS号：586-06-1
• 分子式：C₁₁H₁₇NO₃
• 分子量：211.258
• 相关类别： 原料药 呼吸系统用药 平喘药
• 发布时间：2018-02-20 08:00:00
• 更新时间：2026-07-01 17:10:42
• Metaproterenol (Orciprenaline) 是一种直接作用的拟交感神经药,是 β2-肾上腺素能受体 (β2AR) 激动剂,其 IC50 为 68 nM。Metaproterenol 还具有抗炎活性。

名称

• 中文名: 奥西那林
• 英文名: Orciprenaline
• 中文别名: 肾上腺素杂质43盐酸盐; 5-(1-羟基-2-异丙基氨基乙基)苯-1,3-二酚; 间羟异丙基肾上腺素; 盐酸异丙肾上腺素杂质28
• 英文别名: 1-(3,5-Dihydroxyphenyl)-1-hydroxy-2-isopropylaminoethane; 5-(1-hydroxy-2-propan-2-ylamino-ethyl)benzene-1,3-diol; 5-[1-hydroxy-2-(isopropanylamino)ethyl]benzene-1,3-diol; 1,3-Benzenediol, -hydroxy-2-(1-methylethyl)aminoethyl; 5-[1-hydroxy-2-(1-methylethylamino)ethyl]benzene-1,3-diol; OrciprenalineQ: What is Orciprenaline Q: What is the CAS Number of Orciprenaline Q: What is the storage condition of Orciprenaline Q: What e the applications of Orciprenaline; 5-[2-(Isopropylamino)-1-hydroxyethyl]-1,3-benzenediol; Isoprenaline Hydrochloride Impurity 28; Metaproterenol; 1-(3,5-dihydroxyphenyl)-2-isopropylaminoethanol; 5-[1-Hydroxy-2-(isopropylamino)ethyl]-1,3-benzenediol; 5-[1-Hydroxy-2-(isopropylamino)ethyl]benzene-1,3-diol; Orciprenaline //BP; 3,5-dihydroxy-alpha-((isopropylamino)methyl)benzyl alcohol; Orciprenaline & Orciprenaline Sulfate; 3,5-Dihydroxy-a-[(isopropylamino)methyl]benzyl alcohol; Benzyl alcohol, 3,5-dihydroxy-a-[(isopropylamino)methyl]- (6CI, 8CI); 5-[1-hydroxy-2-(isopropylamino)ethyl]resorcinol; 5-[1-Hydroxy-2-[(1-methylethyl)amino]ethyl]-1,3-benzenediol; 1,3-Benzenediol, 5-[1-hydroxy-2-[(1-methylethyl)amino]ethyl]- (9CI); 1-(3,5-Dihydroxyphenyl)-2-isopropylaminoethanol; 5-(1-hydroxy-2-((1-methylethyl)amino)ethyl)-3-benzenediol; Metaproterenol (base and/or unspecified salts); 3,5-Dihydroxy-a-[(isopropylamino)methyl]benzyl Alcohol; EINECS 209-569-1; inhrine Impurity 43; 3,5-dihydroxy-alpha-((isopropylamino)methyl)-benzyl alcohol; 3,5-Dihydroxy-α-[(isopropylamino)methyl]benzyl alcohol

物化性质

• 密度: 1.2±0.1 g/cm3
• 沸点: 417.5±40.0 °C at 760 mmHg
• 分子式: C₁₁H₁₇NO₃
• 分子量: 211.258
• 闪点: 179.7±17.9 °C
• 精确质量: 211.120850
• PSA: 72.72000
• LogP: 0.13
• 蒸汽压: 0.0±1.0 mmHg at 25°C
• 折射率: 1.579

生物活性

• 描述: Metaproterenol (Orciprenaline) 是一种直接作用的拟交感神经药,是 β2-肾上腺素能受体 (β2AR) 激动剂,其 IC50 为 68 nM。Metaproterenol 还具有抗炎活性。
• 相关类别:
  研究领域 >> 内分泌
• 靶点:

  IC50: 68 nM (β2-adrenergic receptor)[1]

• 体外研究: Metaproterenol(10μM；74小时；THP-1细胞和骨髓巨噬细胞)治疗可增强β-arrestin2及其与高葡萄糖诱导的THP-1细胞和骨髓巨噬细胞中IκBα的相互作用[1]。Metaproterenol(10μM；74小时；THP-1细胞和骨髓巨噬细胞)治疗导致高葡萄糖诱导的THP-1细胞和骨髓巨噬细胞中NF-κB的下调[1]。蛋白质印迹分析[1]细胞系：THP-1细胞和骨髓巨噬细胞浓度：10μM孵育时间：74小时结果：β-arrestin2增强及其与IκBα的相互作用。RT-PCR[1]细胞系：THP-1细胞和骨髓巨噬细胞浓度：10μM孵育时间：74小时结果：导致NF-κB下调。
• 体内研究: 用间蛋白肾治疗Zucker糖尿病性脂肪大鼠12周减弱单核细胞活化以及肾脏和心脏中的促炎和促纤维化反应。因此,间蛋白肾可能对糖尿病肾脏和心血管并发症具有保护作用[1]。
• 参考文献:

  [1]. Noh H, et al. Beta 2-adrenergic receptor agonists are novel regulators of macrophage activation in diabetic renal and cardiovascular complications. Kidney Int. 2017 Jul;92(1):101-113.

  [2]. Ibrahim FA, et al. Highly sensitive spectrofluorimetric method for rapid determination of orciprenaline in biological fluids and pharmaceuticals. Luminescence. 2019 Feb;34(1):77-83.

毒性和生态

CHEMICAL IDENTIFICATION RTECS NUMBER : DO1800000 CHEMICAL NAME : Benzyl alcohol, 3,5-dihydroxy-alpha-((isopropylamino)methyl)- CAS REGISTRY NUMBER : 586-06-1 LAST UPDATED : 199709 DATA ITEMS CITED : 13 MOLECULAR FORMULA : C11-H17-N-O3 MOLECULAR WEIGHT : 211.29 WISWESSER LINE NOTATION : QR CQ EYQ1MY HEALTH HAZARD DATA ACUTE TOXICITY DATA TYPE OF TEST : TDLo - Lowest published toxic dose ROUTE OF EXPOSURE : Oral SPECIES OBSERVED : Human - man DOSE/DURATION : 286 ug/kg TOXIC EFFECTS : Behavioral - tremor Cardiac - arrhythmias (including changes in conduction) Vascular - BP elevation not characterized in autonomic section REFERENCE : AJMSA9 American Journal of the Medical Sciences. (Slack Inc., 6900 Grove Rd., Thorofare, NJ 08086) New series: V.1- 1841- Volume(issue)/page/year: 291,168,1986 TYPE OF TEST : LD50 - Lethal dose, 50 percent kill ROUTE OF EXPOSURE : Oral SPECIES OBSERVED : Rodent - rat DOSE/DURATION : 3370 mg/kg TOXIC EFFECTS : Details of toxic effects not reported other than lethal dose value REFERENCE : TXAPA9 Toxicology and Applied Pharmacology. (Academic Press, Inc., 1 E. First St., Duluth, MN 55802) V.1- 1959- Volume(issue)/page/year: 8,353,1966 TYPE OF TEST : LD50 - Lethal dose, 50 percent kill ROUTE OF EXPOSURE : Intravenous SPECIES OBSERVED : Rodent - rat DOSE/DURATION : 67200 ug/kg TOXIC EFFECTS : Details of toxic effects not reported other than lethal dose value REFERENCE : TXAPA9 Toxicology and Applied Pharmacology. (Academic Press, Inc., 1 E. First St., Duluth, MN 55802) V.1- 1959- Volume(issue)/page/year: 8,353,1966 TYPE OF TEST : LD50 - Lethal dose, 50 percent kill ROUTE OF EXPOSURE : Oral SPECIES OBSERVED : Rodent - mouse DOSE/DURATION : >8130 mg/kg TOXIC EFFECTS : Details of toxic effects not reported other than lethal dose value REFERENCE : TXAPA9 Toxicology and Applied Pharmacology. (Academic Press, Inc., 1 E. First St., Duluth, MN 55802) V.1- 1959- Volume(issue)/page/year: 8,353,1966 TYPE OF TEST : LDLo - Lowest published lethal dose ROUTE OF EXPOSURE : Intraperitoneal SPECIES OBSERVED : Rodent - mouse DOSE/DURATION : 240 mg/kg TOXIC EFFECTS : Autonomic Nervous System - sympathomimetic REFERENCE : APTOA6 Acta Pharmacologica et Toxicologica. (Copenhagen, Denmark) V.1-59, 1945-86. For publisher information, see PHTOEH Volume(issue)/page/year: 31,33,1972 TYPE OF TEST : LD50 - Lethal dose, 50 percent kill ROUTE OF EXPOSURE : Subcutaneous SPECIES OBSERVED : Rodent - mouse DOSE/DURATION : 295 mg/kg TOXIC EFFECTS : Details of toxic effects not reported other than lethal dose value REFERENCE : USXXAM United States Patent Document. (U.S. Patent Office, Box 9, Washington, DC 20231) Volume(issue)/page/year: #4011258 TYPE OF TEST : LD50 - Lethal dose, 50 percent kill ROUTE OF EXPOSURE : Intravenous SPECIES OBSERVED : Rodent - mouse DOSE/DURATION : 86 mg/kg TOXIC EFFECTS : Behavioral - changes in motor activity (specific assay) Cardiac - pulse rate increase, without fall in BP Skin and Appendages - hair REFERENCE : APTOA6 Acta Pharmacologica et Toxicologica. (Copenhagen, Denmark) V.1-59, 1945-86. For publisher information, see PHTOEH Volume(issue)/page/year: 38,474,1976 TYPE OF TEST : LD50 - Lethal dose, 50 percent kill ROUTE OF EXPOSURE : Oral SPECIES OBSERVED : Mammal - dog DOSE/DURATION : 125 mg/kg TOXIC EFFECTS : Details of toxic effects not reported other than lethal dose value REFERENCE : TXAPA9 Toxicology and Applied Pharmacology. (Academic Press, Inc., 1 E. First St., Duluth, MN 55802) V.1- 1959- Volume(issue)/page/year: 8,353,1966 TYPE OF TEST : LD50 - Lethal dose, 50 percent kill ROUTE OF EXPOSURE : Intravenous SPECIES OBSERVED : Mammal - dog DOSE/DURATION : 30 mg/kg TOXIC EFFECTS : Details of toxic effects not reported other than lethal dose value REFERENCE : TXAPA9 Toxicology and Applied Pharmacology. (Academic Press, Inc., 1 E. First St., Duluth, MN 55802) V.1- 1959- Volume(issue)/page/year: 8,353,1966 TYPE OF TEST : LD50 - Lethal dose, 50 percent kill ROUTE OF EXPOSURE : Oral SPECIES OBSERVED : Rodent - rabbit DOSE/DURATION : 3110 mg/kg TOXIC EFFECTS : Details of toxic effects not reported other than lethal dose value REFERENCE : TXAPA9 Toxicology and Applied Pharmacology. (Academic Press, Inc., 1 E. First St., Duluth, MN 55802) V.1- 1959- Volume(issue)/page/year: 8,353,1966 TYPE OF TEST : LD50 - Lethal dose, 50 percent kill ROUTE OF EXPOSURE : Intravenous SPECIES OBSERVED : Rodent - rabbit DOSE/DURATION : 81300 ug/kg TOXIC EFFECTS : Details of toxic effects not reported other than lethal dose value REFERENCE : TXAPA9 Toxicology and Applied Pharmacology. (Academic Press, Inc., 1 E. First St., Duluth, MN 55802) V.1- 1959- Volume(issue)/page/year: 8,353,1966 ** REPRODUCTIVE DATA ** TYPE OF TEST : TDLo - Lowest published toxic dose ROUTE OF EXPOSURE : Oral DOSE : 800 ug/kg SEX/DURATION : female 1 day(s) pre-mating TOXIC EFFECTS : Reproductive - Maternal Effects - uterus, cervix, vagina REFERENCE : RDCNBM Reproduccion. (Madrid, Spain) V.1-7, 1974-83. Discontinued. Volume(issue)/page/year: 5,31,1981 *** NIOSH STANDARDS DEVELOPMENT AND SURVEILLANCE DATA *** NIOSH OCCUPATIONAL EXPOSURE SURVEY DATA : NOES - National Occupational Exposure Survey (1983) NOES Hazard Code - X5007 No. of Facilities: 35 (estimated) No. of Industries: 1 No. of Occupations: 1 No. of Employees: 476 (estimated) No. of Female Employees: 255 (estimated)

制备

【方法一】
3，5-二乙酸基乙酰首先与溴反应，然后与异丙胺反应得过且过-（3，5-二羟基苯基）-2-异丙胺乙酮，将其溶于甲醇，在室温下以镍催化氢化，得异丙喘宁。